Water soluble compounds of cellulose-xantho-fatty acids and method of producing them



Patented Dec. 6, 1932 UNITED STATES.

ATENT-OFFICE LEON LILIENEELD, or VIENNA, AUSTRIA.

WA ER SOLUBLE COMIEOUNDS on cELLnLosn-xAn'rno-FAMY Acrns AND M THOD OF PRODUCING THEM I a I a No Drawing. Application filed January 21, 1926, Serial No. 82,855, and'in Austria February 6, 19 25.

This invention relates to solvents for making solutions of cellulose-xantho-fatty acids and similar bodies described for example in 'my U. S. patent referred to below and in.

British Patent No. 231,800, and relates also to compositions containing such acids or bodies and to new products and to process for bringing such acids and bodies into solution. v

' 7 One object of my invention is to provide a solvent which will dissolve a relatively large proportion of such acids or bodies, whereby relatively strong or concentrated solutions are obtainable for use in the manufacture of artificial material of the nature referred to in the aforementioned United States patent and British. Patent No. 231,800.

Another object of my invention is to produce a solution of such acids or bodies which is stable at room temperature for a considerable period of time. Other objects will apthe description which in presence of water excellent solvents for cellulose-xantho-fatty acids, and that the so.-

lutions of cellulose-xantho-fatty acids in water in the presence of the above described bases, also then show good stability when thebases are employed in excess.

It is immaterial to the process whether and how much the bases themselves are soluble in water. slightly solublebases lead to clear solutions of the cellulose-xantho-fattyacids when they are not employed in excess. Excesses of such bases according to their nature cause turbity of the solutions, which is brought about through emulsion like division inthe solu solutions of 2%, 5%, 8%, or 10% and ab v "can be produced;

in United States Patent No. 1,642,588 or Even water insoluble or tions of the bases, which are for the most part oily. V i

Even very small quantities of the bases sulfice in order to bring the cellulose-xanthofatty acids into solution. As a rule one molecule of the base. sufiices for one molecule of} cellulose-'xantho-fatty acid. According to the nature'of the cellulose-xantho-fatty acid r r The solutions dry to products which are insoluble in water. The resistance of the bodies towateris increased by heating or steaming. F or practicing the process one can mix the bases with water and in this mixture dissolve the cellulose-xantho-fatty acids; or one can mix or knead the cellulose-xantho-fatty acid withwater and then add the base; or one] can 7 mix or knead the cellulose-xantho-fatty acid with the base and then add water.

The cellulose-xantho-fatty acid can begused for the present process in adry or wet state;

E'zv'dmple 1 v 100iparts by weight of'air dried cellulosexantho-acetic acid prepared according'to Ex-v amples 1 or 2 of United States Patent No. 1,642,587 or British Patent No. 231,800 are mixed or kneaded with, 1900 parts by weight of water and treated with 23 parts by weight of monomethyl aniline. Even after short stirring a clear solution is formed, which can be worked up into artificial materials," coatings or the like in the manner as described British Patent No. 231,800.

' mample 2 i parts by weight of cellulose-xanthoacetic acid prepared according to example 2 of theiUnited States Patent No. 1,642,587 are immediately, after the precipitation with sulphuric acid andwashing,lightlyexpressed, so that the expressed residue contains 87.08%

water. 100 parts'by weight of this expressed 95 I residue, corresponding with 13 parts by weight of dry cellulose-xantho-acetic acid are dissolved in a mixture of parts by weight of water and 3 parts by weight of monomethyl aniline. i i. a

There can be used in the foregoing examples, in place of the methyl-aniline, also :1

- mono-alkyl derivative of a toluidine or xylidine.

I ducing said products The phenyl amine alkyl derivatives, such as monomethyl aniline,- dimethyl aniline, monoethyl and diethyl aniline, and like derivatives of the homologues of aniline,l such as toluidine, xylidine etc., are not only excellent solvents for cellulose-xantho-acetic acid but also forall homologues of the same, that is to say also for cellulose-xantho-propionic acid and the like.

Although water has been described as be- 7 ing used with the aromatic amines for dissolving the cellulose-xantho-fatty acids, it is possible to use a mixture of water with alcohol (ethyl or methyl alcohol), acetone and other organic solvents, either singly with water or incombination; However, the addition of considerable quantities ofthe organic solvents named cannotbe generally used, as

precipitation of the celluldse-Xantho-fatty acids will occur. Ethyl or methyl alcohol may be used up to approximately 20%'1n' The solutions prepared according to Examples 1' and 2 last at room 1 months. 7 e e. p The cellulose-xantho-fatty acids, according to the' present invention, combine with the temperature for aromatic amines herein described, forming salts. I Utilizing the reaction between cellulose-xantho-acetic acid and methylaniline as an example, the reactlon of forming the salt- Therefore, utilizing methylaniline inpreparing a solution of a cellulose xantho fatty line cellulose-xantho-acetate. V v The expression cellulose-Xantho-fatty acid occurring in the descriptionand claims includes compounds which are derived from a fatty acid by substituting fora hydrogen atom' united to a carbon atom the residue ofa cellulose-xanthic acid, in which the eelfll'ulose component of the cellulose-xanthic acid may be eitherfcellulose itself or a"con versionfproduct of cellulose or a cellulose compound, that isto. say, products,f for ex} ample, which'm y be bbmined by acting on with the nitrogen of the amine.

a cellulose-xanthic acid with a mono-halogen derivative of a fatty acid, irrespective of whether the cellulose component of the cellulose-xanthic acid is cellulose, or a conversion product or a compound thereof.

Having thus describedmy inventionwhat I claim as new and desire to secure by Letters Patent is 1. The process offorming a water soluble compound from a cellulose-xantho-fatty acid which comprises treating it in the pres. ence of water with an aromatic amine in which a hydrocarbon radical is connected with the nitrogen of the amine. Y 2. The process of forming a water soluble compound from xantho-fatty {acid which comprises treating it in the presenceof water I with an aromaticamine in which a methyl radlcal is connected amine.

acid salt of an alkyl derivative of an aro-' matic amine in which an alkyl radical is connected with the nitrogen of the aminep- 4. A new product, a cellulose-xantho-fatty acid salt of a monoalkyl derivative of an aromatic amine having the alkyl group connect: ed to the nitrogen of the'amine.

A new product, a cellulose-xantho fatty acid saltjof a-N-methyl aniline. 6. A new product, a water soluble salt-o with the nitrogen of the A new product, a cellulose xanthoefatty a cellulose-xantho-fatty acid and a N-alkyl amine, the said salt having the propertyof being stablein water even in the presence of an excess of the'amine. V e

'7. A new product, a cellulos'e-xantho-ace tate of an alkyl derivative of'an aromatic I amine in which an alkyl radical is connected 8. Anew product, a cellulose-x'antho-acetate'of'a monoalkyl derivative of an aromatic amine in which the alkyl group is 'attached to the nitrogen of the amine.

"SLA' new product, tate of N-methyl aniline. V

10. The process of forming a water solublecompound of a cellulose-'xantho-fatty acidwhich comprises treating a cellulose- Xantho-fattyacid in the presence of water with an alkyl derivative off an aromatic amine in which an alkyl radical is connected withthe nitrogen of the amine. 7 e

11. The processof forminga water" soluble compound of a cellulose xantho fatty acid which comprises treating a" cellul-ose- LEON LILIENFELD.

cellulose-xantho-acexan'tho-fatty acid in the presence of water 

